Impact of structural differences in carcinopreventive agents indole-3-carbinol and 3,3′-diindolylmethane on biological activity. An X-ray, 1H–14N NQDR, 13C CP/MAS NMR, and periodic hybrid DFT study
Tài liệu tham khảo
Aggarwal, 2005, Molecular targets and anticancer potential of indole-3-carbinol and its derivatives, Cell cycle (Georgetown, Tex.), 4, 1201, 10.4161/cc.4.9.1993
Ahmad, 2010, Anticancer properties of indole compounds: mechanism of apoptosis induction and role in chemotherapy, Curr. Drug Targets, 11, 652, 10.2174/138945010791170923
Allen, 2002, The Cambridge Structural Database: a quarter of a million crystal structures and rising, Acta Cryst. B, 58, 380, 10.1107/S0108768102003890
Anderton, 2004, Physiological modeling of formulated and crystalline 3,3′-diindolylmethane pharmacokinetics following oral administration in mice, Drug Metab. Dispos., 32, 632, 10.1124/dmd.32.6.632
Antonio, 2014, Phytotherapy in primary health care, Rev. Saude Publica, 48, 541, 10.1590/S0102-311X2007000600021
Arnao, 1996, Indole-3-carbinol as a scavenger of free radicals, Biochem. Mol. Biol. Int., 39, 1125
Aronchik, 2014, The anti-proliferative response of indole-3-carbinol in human melanoma cells is triggered by an interaction with NEDD4-1 and disruption of wild-type PTEN degradation, Mol. Cancer Res., 12, 1621, 10.1158/1541-7786.MCR-14-0018
Auborn, 2003, Lifespan is prolonged in autoimmune-prone (NZB/NZW) F1 mice fed a diet supplemented with indole-3-carbinol, J. Nutr., 133, 3610, 10.1093/jn/133.11.3610
Bailey, 1987, Enhancement of carcinogenesis by the natural anticarcinogen indole-3-carbinol, J. Natl Cancer Inst., 78, 931
Becke, 1993, A new mixing of Hartree–Fock and local density-functional theories, J. Chem. Phys., 98, 1372, 10.1063/1.464304
Bell, 2000, Placebo-controlled trial of indole-3-carbinol in the treatment of CIN, Gynecol. Oncol., 78, 123, 10.1006/gyno.2000.5847
Blinc, 1972, 14N NQR spectroscopy of some amino acids and nucleic bases via double resonance in the laboratory frame, J. Chem. Phys., 57, 5087, 10.1063/1.1678193
Bonnesen, 2001, Dietary indoles and isothiocyanates that are generated from cruciferous vegetables can both stimulate apoptosis and confer protection against DNA damage in human colon cell lines, Cancer Res., 61, 6120
Bradlow, 2008, Review. Indole-3-carbinol as a chemoprotective agent in breast and prostate cancer, In vivo (Athens, Greece), 22, 441
Bradlow, 1999, Multifunctional aspects of the action of indole-3-carbinol as an antitumor agent, Ann. N. Y. Acad. Sci., 889, 204, 10.1111/j.1749-6632.1999.tb08736.x
Brandi, 2003, A new indole-3-carbinol tetrameric derivative inhibits cyclin-dependent kinase 6 expression, and induces G1 cell cycle arrest in both estrogen-dependent and estrogen-independent breast cancer cell lines, Cancer Res., 63, 4028
Burton, 1986, 13C NMR spectra of substituted indoles, Magn. Reson. Chem., 24, 829, 10.1002/mrc.1260240919
Chinni, 2001, Indole-3-carbinol (I3C) induced cell growth inhibition, G1 cell cycle arrest and apoptosis in prostate cancer cells, Oncogene, 20, 2927, 10.1038/sj.onc.1204365
Clark, 2005, CASTEP reference, Z. Krist., 220, 567
Cover, 1998, Indole-3-carbinol inhibits the expression of cyclin-dependent kinase-6 and induces a G1 cell cycle arrest of human breast cancer cells independent of estrogen receptor signaling, J. Bol. Chem., 273, 3838, 10.1074/jbc.273.7.3838
Delley, 1990, An all-electron numerical method for solving the local density functional for polyatomic molecules, J. Chem. Phys., 92, 508, 10.1063/1.458452
Delley, 2000, From molecules to solids with the DMol3 approach, J. Chem. Phys., 113, 7756, 10.1063/1.1316015
Ferlay, 2010, Estimates of worldwide burden of cancer in 2008: GLOBOCAN 2008, Int. J. Cancer, 127, 2893, 10.1002/ijc.25516
Fowke, 2007, Head and neck cancer: a case for inhibition by isothiocyanates and indoles from cruciferous vegetables, Eur. J. Cancer Prev., 16, 348, 10.1097/01.cej.0000236258.80522.fb
Frisch, 2009
Grimme, 2006, Semiempirical GGA-type density functional constructed with a long-range dispersion correction, J. Comput. Chem., 27, 1787, 10.1002/jcc.20495
Hammer, 1999, Improved adsorption energetics within density-functional theory using revised Perdew–Burke–Ernzerhof functionals, Phys. Rev. B, 59, 7413, 10.1103/PhysRevB.59.7413
Hecht, 2000, Inhibition of carcinogenesis by isothiocyanates, Drug Metab. Rev., 32, 395, 10.1081/DMR-100102342
Hexem, 1981, Influence of nitrogen-14 on carbon-13 NMR spectra of solids, J. Am. Chem. Soc., 103, 224, 10.1021/ja00391a057
Higdon, 2007, Cruciferous vegetables and human cancer risk: epidemiologic evidence and mechanistic basis, Pharmacol. Res., 55, 224, 10.1016/j.phrs.2007.01.009
Hsu, 2006, Indole-3-carbinol mediated cell cycle arrest of LNCaP human prostate cancer cells requires the induced production of activated p53 tumor suppressor protein, Biochem. Pharmacol., 72, 1714, 10.1016/j.bcp.2006.08.012
Jin, 1999, Indole-3-carbinol prevents cervical cancer in human papilloma virus type 16 (HPV16) transgenic mice, Cancer Res., 59, 3991
Kelloff, 2000, Perspectives on cancer chemoprevention research and drug development, Adv. Cancer Res., 78, 199, 10.1016/S0065-230X(08)61026-X
Kohn, 1965, Self-consistent equations including exchange and correlation effects, Phys. Rev., 140, A1133, 10.1103/PhysRev.140.A1133
Kristal, 2002, Brassica vegetables and prostate cancer risk: a review of the epidemiological evidence, Nutr. Cancer, 42, 1, 10.1207/S15327914NC421_1
Kwon, 2007, Cancer chemoprevention by phytochemicals: potential molecular targets, biomarkers and animal models, Acta Pharmacol. Sin., 28, 1409, 10.1111/j.1745-7254.2007.00694.x
Landis-Piwowar, 2014, Cancer chemoprevention: current state of the art, Cancer Growth Metastasis, 7, 19, 10.4137/CGM.S11288
Latosińska, 2003, NQR parameters: electric field gradient tensor and asymmetry parameter studied in terms of density functional theory, Int. J. Quant. Chem., 91, 284, 10.1002/qua.10451
Latosińska, 2005, Structure–activity study of thiazides by magnetic resonance methods (NQR, NMR, EPR) and DFT calculations, J. Mol. Graph. Model., 23, 329, 10.1016/j.jmgm.2004.11.001
Latosińska, 2007, Applications of nuclear quadrupole resonance spectroscopy in drug development, Expert Opin. Drug Discov., 2, 225, 10.1517/17460441.2.2.225
Latosińska, 2000, Analysis of the NQR parameters in 2-nitro-5-methylimidazole derivatives by quantum chemical calculations, Phys. Chem. Chem. Phys., 2, 145, 10.1039/a906295e
Latosińska, 2013, Anticancer drug discovery—from serendipity to rational design, 35
Latosińska, 2014, Quantum-chemical insight into structure–reactivity relationship in 4,5,6,7-tetrahalogeno-1H-benzimidazoles: a combined X-ray, DSC, DFT/QTAIM, Hirshfeld surface-based, and molecular docking approach, J. Phys. Chem. A, 118, 2089, 10.1021/jp411547z
Latosińska, 2014, Topology of the interactions pattern in pharmaceutically relevant polymorphs of methylxanthines (caffeine, theobromine, and theophylline): combined experimental (1H–14N nuclear quadrupole double resonance) and computational (DFT and Hirshfeld-based) study, J. Chem. Inf. Model., 54, 2570, 10.1021/ci5004224
Latosińska, 2014, An insight into prototropism and supramolecular motifs in solid-state structures of allopurinol, hypoxanthine, xanthine, and uric acid. A 1H–14N NQDR spectroscopy, hybrid DFT/QTAIM, and Hirshfeld surface-based study, J. Phys. Chem. B, 118, 10837, 10.1021/jp504871y
Lee, 2003, Beneficial and adverse effects of chemopreventive agents, Mutat. Res., 523–524, 265, 10.1016/S0027-5107(02)00342-1
Lee, 1988, Development of the Colle–Salvetti correlation-energy formula into a functional of the electron density, Phys. Rev. B, 37, 785, 10.1103/PhysRevB.37.785
Levy, 1979, Universal variational functionals of electron densities, first-order density matrices, and natural spin-orbitals and solution of the v-representability problem, Proc. Natl. Acad. Sci. USA, 76, 6062, 10.1073/pnas.76.12.6062
Licznerska, 2013, Modulation of CYP19 expression by cabbage juices and their active components: indole-3-carbinol and 3,3′-diindolylmethene in human breast epithelial cell lines, Eur. J. Nutr., 52, 1483, 10.1007/s00394-012-0455-9
Machijima, 2009, Anti-adult T-cell leukemia/lymphoma effects of indole-3-carbinol, Retrovirology, 6, 7, 10.1186/1742-4690-6-7
Maciejewska, 2005, Structure in solid state of 3,3′-diindolylmethane derivatives, potent cytotoxic agents against human tumor cells, followed X-ray diffraction and 13C CP/MAS NMR analyses, J. Mol. Struct., 753, 53, 10.1016/j.molstruc.2005.05.035
Maciejewska, 2006, DNA-based electrochemical biosensors for monitoring of bis-indoles as potential antitumoral agents, chemistry, X-ray crystallography, Bioelectrochemistry, 69, 1, 10.1016/j.bioelechem.2005.09.003
Markushin, 2003, Spectral characterization of catechol estrogen quinone (CEQ)-derived DNA adducts and their identification in human breast tissue extract, Chem. Res. Toxicol., 16, 1107, 10.1021/tx0340854
Mehring, 1983
Monkhorst, 1976, Special points for Brillouin-zone integrations, Phys. Rev. B, 13, 5188, 10.1103/PhysRevB.13.5188
Morzyk-Ociepa, 2004, Structures and vibrational spectra of indole carboxylic acids. Part I. Indole-2-carboxylic acid, J. Mol. Struct., 688, 79, 10.1016/j.molstruc.2003.09.027
Murillo, 2001, Cruciferous vegetables and cancer prevention, Nutr. Cancer, 41, 17, 10.1080/01635581.2001.9680607
Perdew, 1996, Generalized gradient approximation made simple, Phys. Rev. Lett., 77, 3865, 10.1103/PhysRevLett.77.3865
Perdew, 2008, Restoring the density-gradient expansion for exchange in solids and surfaces, Phys. Rev. Lett., 100, 136406, 10.1103/PhysRevLett.100.136406
Pickard, 2001, All-electron magnetic response with pseudopotentials: NMR chemical shifts, Phys. Rev. B, 63, 245101, 10.1103/PhysRevB.63.245101
Politzer, 2001, Molecular surface electrostatic potentials in relation to noncovalent interactions in biological systems, Int. J. Quantum Chem., 85, 676, 10.1002/qua.1706
Poornima, 2014, Regulation of carbohydrate metabolism by indole-3-carbinol and its metabolite 3,3′-diindolylmethane in high-fat diet-induced C57BL/6J mice, Mol. Cell. Biochem., 385, 7, 10.1007/s11010-013-1808-2
Pyykkö, 2008, Year-2008 nuclear quadrupole moments, Mol. Phys., 106, 1965, 10.1080/00268970802018367
Raj, 2008, Synergistic action of dietary phyto-antioxidants on survival and proliferation of ovarian cancer cells, Gynecol. Oncol., 110, 432, 10.1016/j.ygyno.2008.05.001
Reed, 2005, A phase I study of indole-3-carbinol in women: tolerability and effects, Cancer Epidemiol. Biomarkers Prev., 14, 1953, 10.1158/1055-9965.EPI-05-0121
Roychowdhury, 1975, The crystal structure of indole, Acta Cryst. B, 31, 1559, 10.1107/S0567740875005687
Sarkar, 2004, Indole-3-carbinol and prostate cancer, J. Nutr., 134, 3493, 10.1093/jn/134.12.3493S
Seliger, 2008, Measurement of the 14N nuclear quadrupole resonance frequencies by the solid effect, J. Magn. Reson., 193, 54, 10.1016/j.jmr.2008.04.020
Seliger, 2008, Sensitivity of nuclear-quadrupole double-resonance detection of half-integer spin nuclei, J. Magn. Reson., 194, 175, 10.1016/j.jmr.2008.06.021
Seliger, 2012, New methods for detection of 14N NQR frequencies, Appl. Magn. Reson., 43, 469, 10.1007/s00723-011-0303-8
Seliger, 1976, Proton-14N double resonance study of the structural phase transitions in the perovskite type layer compound (CH3NH3)2CdCl4, Z. Phys. B, 25, 189, 10.1007/BF01320180
Seliger, 1994, 1H–14N nuclear quadrupole double resonance with multiple frequency sweeps, Z. Naturforsch., 49, 1
Seliger, 1994, A new highly sensitive 1H–14N nuclear-quadrupole double-resonance technique, J. Magn. Reson. A, 106, 214, 10.1006/jmra.1994.1027
Sheldrick, 2008, A short history of SHELX, Acta Cryst. A, 64, 112, 10.1107/S0108767307043930
Singh, 2006, Mechanisms of action of novel agents for prostate cancer chemoprevention, Endocr. Relat. Cancer, 13, 751, 10.1677/erc.1.01126
Smith, 2003, Indole-3-carboxylic acid, Acta Cryst. E, 59, o1766, 10.1107/S1600536803022670
Spackman, 2009, Hirshfeld surface analysis, CrystEngComm, 11, 19, 10.1039/B818330A
Spackman, 2002, Fingerprinting intermolecular interactions in molecular crystals, CrystEngComm, 4, 378, 10.1039/B203191B
Tkatchenko, 2009, Accurate molecular van der Waals interactions from ground-state electron density and free-atom reference data, Phys. Rev. Lett., 102, 073005, 10.1103/PhysRevLett.102.073005
Weng, 2008, Indole-3-carbinol as a chemopreventive and anti-cancer agent, Cancer Lett., 262, 153, 10.1016/j.canlet.2008.01.033
Wishart, 2007, HMDB: the human metabolome database, Nucleic Acids Res., 35, D521, 10.1093/nar/gkl923
Wong, 1997, Dose-ranging study of indole-3-carbinol for breast cancer prevention, J. Cell. Biochem., 28–29, 111, 10.1002/(SICI)1097-4644(1997)28/29+<111::AID-JCB12>3.0.CO;2-K
Wu, 2006, More accurate generalized gradient approximation for solids, Phys. Rev. B, 73, 235116, 10.1103/PhysRevB.73.235116
X1, 2010. X1. Oxford Diffraction CrysAlisPro: Data Collection and Processing Software for X-Ray Diffractometers GUI, Version 4. Agilent Technologies, Santa Clara, CA.
Yan, 2009, Indole-3-carbinol improves survival in lupus-prone mice by inducing tandem B- and T-cell differentiation blockades, Clin. Immunol., 131, 481, 10.1016/j.clim.2009.01.013
Zhang, 2003, Indole-3-carbinol induces a G1 cell cycle arrest and inhibits prostate-specific antigen production in human LNCaP prostate carcinoma cells, Cancer, 98, 2511, 10.1002/cncr.11844